Pergamon
Tetrahedron Letters 39 (1998) 3555-3558
TETRAHEDRON
LETTERS
Aldoi Condensations Catalysed by Novel Mg-Al-O-t-Bu
Hydrotalcite
B.M. Choudar~*', M. Lakshmi Kantam °, B. Kavita', Ch. Venkat Reddy',
K.Koteswara Rao" and F. Figueras b
"Indian Institute of Chemical Technology, Hyderabad- 500007, India
b Institut dc Recherehes mr la Catalyse, 2, Avenue Albert Einstein
69626 Villeurbanne cedex - France
Received 12 January 1998; revised 5 March 1998; accepted 6 March 1998
Abstract: A novel Mg-AI-O-t-Bu hydrotalcite prepared for the first time, catalyses
condensation reactions selectively to aldols (3) at 0°C in quantitative yields.
© 1998 ElsevierS :ience Ltd. All rights reserved.
There has bq~en increasing attention on the design and use of environmentally
compatible solid acid-base catalysts targeted to minimise the emission of effluents in
chemical industries. These solid acid-base catalysts can be easily separated and recycled.
Layered double hydroxides (LDHs) or hydrotalcite like compounds (HTLCs) have
recently received considerable commercial interest ~ as adsorbents, anion exchangers and
most important as base catalysts 2"4. Hydrotalcites are represented by the formula
[M2÷(1-x)M~÷ x(OHh] x÷(A ~- x/m).nH20, where the M 2+ are the divalent ions and M 3+ are
the trivalent ions. The compensating anions may be Off, CI', NOr, COl etc. and on their
expulsion at 450°C, LDHs gives a highly active homogeneous mixed oxide which is
potentially a basic catalyst for a variety of organic transformations such as aldol
condensation s, olefin isomerization2, epoxidations of activated olefins with hydrogen
peroxide 6, alkylations of diketones 7, nucleophilic halide exchange s and Clalsen-Schmidt
condensation 9 etc.
The aldol condensation is of prime importance for fine chemical synthesis and is
generally catalysed b) acids or bases t°, In the laboratory, many catalysts have been
reported such as alumirtan'~2, zeolites 13, sepiolite ~4, and hydrotalcites 9"is. The reported
works ~'7'm~6 on aldolisations were performed at relatively high temperatures. Earlier, we
designed and developod modified hydrotalcite by incorporation of hydroxyls during the
rehydration process aud found it to be excellent for aldol condensation ~7. Now, we opted
a novel approach of in.:orporation of tert-butoxide by an exchange process, to tune up the
hydrotalcite for higher basicity. We report in this letter the preparation of Mg-AI-O-t-Bu
hydrotalcite and selective condensations to aldol products
0040-4039/98/$19.00 © 1998 Elsevier Science Ltd. All rights reserved.
PII: S0040-4039(98)00547-4